Heliangin (CHEM030352)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:50:22 UTC
Update Date2016-11-09 01:19:03 UTC
Accession NumberCHEM030352
Identification
Common NameHeliangin
ClassSmall Molecule
DescriptionA sesquiterpene lactone of the heliangolide group isolated from Eupatorium kiirunense and Calea rotundifolia and exhibits cytotoxicity against human oral epidermoid (KB), cervical epitheloid (Hela) and liver (hepa59T/VGH) carcinoma cells.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
HeliangineHMDB
LeptocarpinHMDB
(9Z)-8-Hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoic acidGenerator
HelianginMeSH
Leptocarpin, (1ar-(1ar*,3S*,4Z,5ar*,8ar*,9R*(e),10ar*))-isomerMeSH
Leptocarpin, (1ar-(1ar*,3S*,4Z,5as*,8ar*,9S*,10ar*))-isomerMeSH
Chemical FormulaC20H26O6
Average Molecular Mass362.417 g/mol
Monoisotopic Mass362.173 g/mol
CAS Registry Number13323-48-3
IUPAC Name(9Z)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate
Traditional Name(9Z)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate
SMILESC\C=C(/C)C(=O)OC1CC2(C)OC2CC(O)\C(C)=C/C2OC(=O)C(=C)C12
InChI IdentifierInChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6+,11-7-
InChI KeyDZTWAOVNNLDWNH-QZTBCQRESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Sesquiterpenoid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Fatty acyl
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP1.45ALOGPS
logP2.41ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.22ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area85.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.54 m³·mol⁻¹ChemAxon
Polarizability38.36 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053s-9014000000-d4115525398926b17407Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-053r-9001100000-6a89a281481d94379912Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-2039000000-785f137b68ea1b583520Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06us-9184000000-645c0c1af1c3e2495ce8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-9120000000-35228986d558858a4334Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-399bd5ed523ca36c8d99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0901-5049000000-604186f0c012089dab02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f81-9550000000-3dfd2150bf626a73e577Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2092000000-a2107e87fa08cd77bbc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-9060000000-90926566628c185acbffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-2090000000-7d965b00d72ca32904cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-be4f1c6baa4bb8ca15a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0094000000-6fae0e8f2a70227265cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-7098000000-677ea1d7babf76468eb6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00000235
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID28532736
ChEBI ID5638
PubChem Compound ID70697714
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15921421